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Tetramethyl orthosilicate (TMOS) as a reagent for direct amidation of carboxylic acids

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Title: Tetramethyl orthosilicate (TMOS) as a reagent for direct amidation of carboxylic acids
Authors: Braddock, DC
Lickiss, P
Rowley, B
Pugh, DC
Purnomo
Santhakumar, G
Fussell, S
Item Type: Journal Article
Abstract: Tetramethyl orthosilicate (TMOS) is shown to be an effective reagent for direct amidation of aliphatic and aromatic carboxylic acids with amines and anilines. The amide products are obtained in good to quantitative yields in pure form directly after workup without the need for any further purification. A silyl ester as the putative activated intermediate is observed by NMR methods. Amidations on a 1 mol scale are demonstrated with a favorable process mass intensity.
Issue Date: 2-Feb-2018
Date of Acceptance: 30-Jan-2018
URI: http://hdl.handle.net/10044/1/56706
DOI: 10.1021/acs.orglett.7b03841
ISSN: 1523-7052
Publisher: American Chemical Society
Start Page: 950
End Page: 953
Journal / Book Title: Organic Letters
Volume: 20
Issue: 4
Copyright Statement: This is an open access article published under a Creative Commons Attribution (CC-BY) License, which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
Sponsor/Funder: Engineering & Physical Science Research Council (EPSRC)
Funder's Grant Number: EP/P030742/1
Keywords: Science & Technology
Physical Sciences
Chemistry, Organic
Chemistry
AMIDE BOND FORMATION
CATALYZED DIRECT AMIDATION
ROOM-TEMPERATURE
MESOPOROUS SILICA
PEPTIDE-SYNTHESIS
COUPLING REAGENT
CONVENIENT METHOD
AMINO-ACIDS
IN-SITU
CARBOXAMIDES
Organic Chemistry
03 Chemical Sciences
Publication Status: Published
Online Publication Date: 2018-02-02
Appears in Collections:Chemistry
Faculty of Natural Sciences